tetraethyl 1-butoxymethylene-1,1-bisphosphonate | 103424-77-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetraethyl 1-butoxymethylene-1,1-bisphosphonate
• 英文别名: tetraethyl (n-butoxymethylene)-bisphosphonate；1-[bis(diethoxyphosphoryl)methoxy]butane
• CAS: 103424-77-7
• 化学式: C₁₃H₃₀O₇P₂
• 分子量: 360.325
• InChiKey: FCUKQLCAKJXJCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tetraethyl 1-butoxymethylene-1,1-bisphosphonate 在 盐酸 作用下， 反应 10.0h， 生成 (n-butoxymethylene)-bisphosphonic acid
  参考文献：
  名称：

  Ollivier; Sturtz; Legendre, European Journal of Medicinal Chemistry, 1986, vol. 21, # 2, p. 103 - 110

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl butoxymethylphosphonate 、 氯磷酸二乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以87%的产率得到tetraethyl 1-butoxymethylene-1,1-bisphosphonate
  参考文献：
  名称：

  Synthesis of functionalized alkoxyalkylidene gem-bisphosphonates

  摘要：

  We report the synthesis of a series of new functionalized bisphosphonates and bisphosphonic acids with an alkoxy group fixed at the geminal carbon, which is proposed to increase their lipophilicity and so their bioavailability. Subsequently, the alkylation of these alkoxy bisphosphonates with allyl bromide is reported. The reactivity of the allyl group has been studied to give access to alkoxy bisphosphonates functionalized by diverse groups including alcohol, aldehyde, carboxylic acid, epoxide and amine. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.052

文献信息

• Bisphosphonic acids and esters
  申请人：Leo Pharmaceutical Products, Ltd.

  公开号：US04732998A1

  公开（公告）日：1988-03-22

  The present invention relates to hitherto unknown compounds of the formula I ##STR1## in which R.sub.1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C.sub.1 -C.sub.10 hydrocarbon radical, an aryl or an aryl-C.sub.1 -C.sub.4 -alkyl radical, R.sub.1 if desired being unsubstituted or substituted with straight or branched C.sub.1 -C.sub.4 -alkyl, amino, C.sub.1 -C.sub.4 -alkamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino, carboxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, hydroxy, C.sub.1 -C.sub.4 -alkoxy, phenoxy, mercapto, C.sub.1 -C.sub.4 -alkylthio, phenylthio, halogen, trifluoromethyl; R.sub.2 stands for hydrogen, C.sub.1 -C.sub.8 -alkyl, aryl-C.sub.1 -C.sub.4 -alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the proviso that R.sub.2 cannot be hydrogen or methyl if n=O and R.sub.1 is methyl. The compounds of the invention are valuable in the human and veterinary practice.

  本发明涉及迄今为止未知的化合物，其化学式为I，在该式中，R.sub.1是直链或支链、饱和或不饱和的脂肪族或脂环族C.sub.1-C.sub.10烃基，芳基或芳基-C.sub.1-C.sub.4-烷基基团，R.sub.1如有必要，可以是未取代的或取代的，取代基为直链或支链C.sub.1-C.sub.4-烷基，氨基，C.sub.1-C.sub.4-烷氨基，二-(C.sub.1-C.sub.4-烷基)-氨基，羧基，C.sub.1-C.sub.4-烷氧羰基，羟基，C.sub.1-C.sub.4-烷氧基，苯氧基，巯基，C.sub.1-C.sub.4-烷硫基，苯硫基，卤素，三氟甲基；R.sub.2代表氢、C.sub.1-C.sub.8-烷基，芳基-C.sub.1-C.sub.4-烷基或卤素；X为氧或硫，n为0到2的整数；但R.sub.2不能为氢或甲基，如果n=0且R.sub.1为甲基。本发明的化合物在人类和兽医实践中具有重要价值。
• OLLIVIER, R.;STURTZ, G.;LEGENDRE, J. -M.;JACOLOT, G.;TURZO, A., EUR. J. MED. CHEM., 1986, 21, N 2, 103-110
  作者：OLLIVIER, R.、STURTZ, G.、LEGENDRE, J. -M.、JACOLOT, G.、TURZO, A.

  DOI：——

  日期：——
• Synthesis of functionalized alkoxyalkylidene gem-bisphosphonates
  作者：Jean-Pierre Haelters、Hélène Couthon-Gourvès、Alan Le Goff、Gaelle Simon、Bernard Corbel、Paul-Alain Jaffrès

  DOI：10.1016/j.tet.2008.04.052

  日期：2008.6

  We report the synthesis of a series of new functionalized bisphosphonates and bisphosphonic acids with an alkoxy group fixed at the geminal carbon, which is proposed to increase their lipophilicity and so their bioavailability. Subsequently, the alkylation of these alkoxy bisphosphonates with allyl bromide is reported. The reactivity of the allyl group has been studied to give access to alkoxy bisphosphonates functionalized by diverse groups including alcohol, aldehyde, carboxylic acid, epoxide and amine. (c) 2008 Elsevier Ltd. All rights reserved.
• Ollivier; Sturtz; Legendre, European Journal of Medicinal Chemistry, 1986, vol. 21, # 2, p. 103 - 110
  作者：Ollivier、Sturtz、Legendre、et al.

  DOI：——

  日期：——